Tetrahedron p. 3073 - 3078 (1982)
Update date:2022-09-26
Topics:
Harger, Martin J. P.
Westlake, Sally
When an alkylphenylphosphinic azide RPhP(O)N3 (R=Me, Et, Pri or But) is photolysed in MeOH either the alkyl or phenyl group can migrate from P to N in the Curtius-like rearrangement.The composition of the product shows that migration of the alkyl group R is preferred.However, the preference is not great and decreases as R changes But->Pri->Et->Me-> (approx. migratory aptitudes relative to Ph: 2.1, 1.7, 1.3, 1.2 respectively), probably because the Ph-P bond is better able to assume the correct conformation for Ph migration when R is less bulky.For t-butylmethylphosphinic azide there is very little preference for migration of But relative to Me.Small amounts of unrearranged products such as ButPhP(O)NHOMe and ButPhP(O)NH2 are generally produced in the photolyses, together with the methyl phosphinates RPhP(O)OMe (major product when R=Me) resulting from (non-photochemical) solvolysis of the azide.
View MoreZhenjiang Haitong Chemical Industry Co., Ltd.
Contact:+86 (511) 8448-0369
Address:Baoyan Town, Dantu District, Zhenjiang City, Jiangsu, China
Hunan Warrant Chiral Pharmaceutical Co., Ltd.
website:http://www.hwcpharm.com
Contact:+86-0731-85910593
Address:LuTian Road No.28
Suzhou Sinosun Imp.&Exp. Corporation
website:http://www.szsinosun.com
Contact:+86-512-63488895,63488616
Address:No.758 East Jiangling Road Wujiang Economic & Technological Developmenty Zone Jiangsu China
Beijing Mediking Biopharm Co., Ltd.
Contact:+86-10-89753524/81760121/81769521
Address:Hongxianghong Incubator, Beiqijia Town, Changping district, Beijing, China
Yingkou Sanzheng New Technology Chemical Industry Co., Ltd.
Contact:+86-417-2927806
Address:yingkou
Doi:10.1021/ja01631a048
(1954)Doi:10.1080/10426507.2010.546587
(2011)Doi:10.1021/ja01353a030
(1931)Doi:10.1002/ejoc.200400799
(2005)Doi:10.1021/ja01339a043
(1933)Doi:10.1016/j.bmcl.2016.12.046
(2017)